Drew is the main protagonist of the series. He is a perpetual "nice guy." For most of the series, he works in the human resources department of Winfred-Lauder, a multinational department store chain. He's portrayed as a lovable loser, though he's the most successful of his group of friends. Drew is the founder and co-owner of Buzz Beer, a special coffee-containing brew. He has a long-standing feud with Mimi Bobeck; his pranks have included destroying her clothes, shredding her vacation requests, and masquerading as Antonio Banderas to taunt her. Drew is also a fan of the Cleveland Indians, Cleveland Cavaliers, and the Cleveland Browns.

In Season One, they work for the unseen Mr. Bell (Kevin Pollak), only seen in the season one finale, to which he is greeted with applause; in later seasons, their boss and sometimes-co-worker is Nigel Wick (Craig Ferguson), an eccentric, sadistic and unlucky Englishman. In the final two seasons, they work for peaceful, hippie-like Evan (Kyle Howard) and the much more professional Scott (Jonathan Mangum), tech-smart but naïve twenty-somethings who own the Neverending Store, an online retailer with offices in the same location.

In addition to his day job, Drew, along with Oswald Harvey, Lewis Kiniski, and Kate O'Brien (replaced from around Season 5 onwards by Mimi, runs a small business out of his garage, selling Buzz Beer, a caffeinated alcoholic drink. It becomes popular in the region and is sold at the group's hangout, The Warsaw Tavern.